The imidazolidin-2,4-dione compound is a compound useful for, for example, a material for decomposing a harmful halogenated aromatic hydrocarbon compound such as dioxin, etc. (for example, see Patent Literature 1), an electroless silver plating solution for electronic parts (for example, see Patent Literature 2) or a diazo copying material (for example, see Patent Literature 3), etc.
There has been disclosed a method for producing 1,3-dimethyl-imidazolidin-2,4-dione by reacting 1,3-dimethyl-4,5-dihydroxy-2-imidazolidinone and formic acid under reflux (for example, see Patent Literature 4). However, according to this method, it needs to use a large amount of formic acid which is harmful to skin or eyes, and causes bad effects on a living body such as liver, kidney, etc., by chronic exposure. Moreover, the treatment after the reaction is complicated, so that there were problems on working procedure and production as an industrial manufacturing method of an imidazolidin-2,4-dione compound.
Also, the above-mentioned 1,3-dimethyl-4,5-dihydroxy-2-imidazolidinone is useful as a synthetic intermediate or a starting material for medicines and agricultural chemicals other than for the preparation of the 1,3-dimethyl-imidazolidin-2,4-dione.
As a preparation method of the compound, a method of reacting glyoxal and 1,3-dimethylurea in water in the presence of a base to obtain an aqueous solution of 4,5-dihydroxy-1,3-dimethyl-2-imidazolidinone, and removing water from the aqueous solution to isolate 4,5-dihydroxy-1,3-dimethyl-2-imidazolidinone has conventionally been disclosed (for example, see Non-Patent Literature 1). However, distillation of water accompanies danger in bumping, etc., and a huge amount of heat energy is required due to large specific heat of water, whereby it was not a satisfactory method as an industrially practical method.
Patent Literature 1: JP 2006-192114A
Patent Literature 2: JP 2000-160351A
Patent Literature 3: JP 57-124728A
Patent Literature 4: JP 11-158155A
Non-Patent Literature 1: J. Org. Chem., 30, 2179 (1965)